


Shuichi Saihara x reader first time

by M-Y-Fandoms (M_Y_Fandoms)



Category: Dangan Ronpa - All Media Types, New Dangan Ronpa V3: Everyone's New Semester of Killing
Genre: Awkward Sexual Situations, Awkwardness, Childhood Friends, Confessions, Cute, Established Relationship, Explicit Sexual Content, F/M, Female Reader, First Kiss, First Time, First Time Sex, Fluff, Friends to Lovers, Gen, Gender-Neutral Pronouns, Innocence, Lemon, Loss of Virginity, Love Confessions, M/M, Male - Freeform, Multi, NSFW, Other, Reader Insert, Sex, female - Freeform, gender neutral reader, killing game, male reader - Freeform, virgin, x Reader, y/n, your name
Language: English
Status: Completed
Published: 2020-09-04
Updated: 2020-09-04
Packaged: 2021-03-06 16:28:35
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,345
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26291911
Author URL: https://archiveofourown.org/users/M_Y_Fandoms/pseuds/M-Y-Fandoms
Summary: A request from my Danganronpa themed reader insert Tumblr blog please follow us there for more Danganronpa one-shots/imagines/headcanons/nsfw/most to least likely lists/fluff and angst, plus they go up there first so you’d see them faster and be able to request your own there for me to write.@danganronpa-x-reader on tumblr. Please go follow!Summary: Shuichi’s first time with his childhood best friend. Expect awkward, fluffy innocent virgin sex. Super cute and established with plot
Relationships: Saihara Shuichi/Reader
Comments: 6
Kudos: 209





	Shuichi Saihara x reader first time

This killing game was hard on everyone, but you and Shuichi had a leg up that put everyone else at a bit of a disadvantage: you knew each other before. Yes, Saihara fortunately attended the same elementary, middle, and high-school as you. He was a childhood friend. Your parents were drinking buddies and became close soon after you moved into the same neighborhood. However, when you both awoke in this high-school of horrors, you couldn’t remember anything after freshman year. What happened after then… remained shrouded in mystery. How did you get here? Why were you far older in age than in your most recent memory? Who were these other students?

You and Shuichi often spent time together alone, trying to figure out why you two knew each other when no one else did. In the darkest times, when despair tried to get you both down, you’d hug him and bring up that time in kindergarten when he peed his pants because he was too scared to ask the teacher to use the restroom. He’d blush, humiliated but distracted from current events, nonetheless.

When Monokuma announced a dead body, after the long and draining trial, you’d lean against his chest on his bed as he tried to shut himself out, tried to sink deeper into his melancholy, and you’d bring up middle school. Remember when you screamed at the teacher for forcing you to take off your hat? Of course he did. You were so proud of him for finally taking it off here at the Ultimate Academy, his posture a bit prouder and straighter. He was… more handsome than you remember.

Now, it was late into the night, maybe 2 am, and you sat there, with your old friend in the library, reading and just chatting about the stressors of the day. You scanned his face every so often as he spoke: his soft lips, his beautifully long lashes. Over the years his dorky, bowl-like haircut had grown out into long, soft, navy-colored tresses, and some strands hung in his face. He blushed, cracking a crooked, awkward grin upon noticing you staring. He looked down as always, and not into your eyes.

“(Y-Y/N)?” He spoke softly. You shook yourself back to the present.

“Yeah?” You sputtered.

“I asked how you were doing, after yesterday’s trial…?”

“Oh, uh… about as well as you’d expect, but I’m glad you’re here with me.” you smiled gently.

“I’m always with you,” he stated plainly.

“And I wouldn’t have it any other way, Saihara. You’re my best friend, after all. I love you!” His eyes widened to the size of two moons. “L-like a brother, I mean!” His cheeks flushed a deep red as he looked into his lap, and you went silent, feeling a bit guilty for flustering him so suddenly.

He chuckled weakly to fill the silence of the dimly lit, empty library. It was a habit of his when things got awkward, and you knew when he was feeling it. You and Shuichi were always very close, but you couldn’t remember starting to develop this little crush on him until late into middle school. It felt odd, wrong, even. You knew you were like a sister to him, too. A confidant and someone there for emotional and physical comfort, but not romantic.

“I was wondering, Shuichi…” you changed the subject, and he looked to you again. “Tomorrow night, I’m playing some stupid video game with Kokichi and Gonta in the AV room next door. I got roped into it, but Kokichi said I’d need to find my own partner by then… will you be mine?”

He tensed up, not really knowing what to say. He set down the book in his hands to think. He wasn’t good with situations like this, and though you hung out every day, it was kind of unspoken, a habit. You never specifically asked for his company. He felt warm and fuzzy, wanted… and worried.

What should I say? What do I do now… he spoke internally to himself. I’m horrible at video games, I can’t just say no, that’s rude, and Y/N knows I have no reason to refuse. I mean, of course I wanna but… I like Y/N a lot… and I’ll look like a complete fool! Fumbling with the controls an-

"Shuichi….“ You gave him a puzzled look. He had just been sitting there for a full minute with a blank look on his face. "It’s okay, you know, if you don’t want t-”

"No!“ He reached a hand toward you and it hovered in mid-air. "I’ll- I’ll go with you… I’d l-love to,” His voice shook. He sounded very hesitant, but you smiled.

"Ok! Yay!” Your eyes crinkled into a relieved smile, and he returned it, but you could tell underneath it all, your precious blue-haired angel was quite stressed and nervous. As you both fell back into reading, he wore a distressed, almost pained expression.

~

"That last trial was something else…” Around half an hour passed since either of you had last spoken, and you were growing bored of the novel in your hands. You chuckled, crossing your arms and looking thoughtfully into the ceiling as you stood and stretched. “Heh, you know, I know we don’t technically know what the people in the outside world are doing, but I envy them anyway… they’re all free out there, probably in some office cubicle or safe at home with their families…” you sighed, Shuichi listening casually, still flipping through his book. “They don’t even know we’re trapped here… I mean, maybe they do, but they sure aren’t in any hurry to save us, huh? I think about it often here, how our lives are most likely going to be cut short? I mean,” you chuckled cynically, “I’ll probably die here before I get my first kiss…” Shuichi was interested now. He slowly closed the book, his eyes studying you intensely. “Wh-what?” You noticed him staring and asked, heart skipping a beat.

"What you said… you’ve never kissed anyone?“ Shuichi questioned curiously.

"Why, have you?” You looked down innocently and batted your eyelashes.

"Well, no, b-but…“

"WHAT?!” You laughed out loud, holding your ribs, “Shuichi, how old are you now?! And you haven’t kissed anyone yet?!“ You howled viciously. Shuichi’s face contorted painfully.

"But you-?!”

“Shuichi! I was joking! I would think you’d know that, being my best friend for so long!” Was he just that oblivious?

“W-well I don’t know! I’m not actually always with you!” He retorted, frustrated with your teasing.

“Of course I’ve kissed someone before! I was just exaggerating! I just meant I’ll probably die young and long before anyone our age on the outside. Have you seriously never kissed anyone?!”

"Well, N-no… of c-course not…“ Shuichi’s face now was an absurd shade of crimson. He played with his hands and looked away from you in complete and utter embarrassment. "S-so?”

"Well what do you mean ‘of course not’? Why woul-“ You caught yourself, a wave of anxiety washing over you. You almost just revealed yourself to him, and keeping quiet would save you the humiliation.

"Why w-what?” He brushed his hair back and out of his face. Well now you’d have to tell him.

"I was gonna say…“ you hesitated,” why wouldn’t someone w-wanna kiss you?“ You said the last part almost inaudibly. "I mean, you’re cute, you’re so intelligent, loyal, and kind to everyone. Why’d you make it sound like no one would ever even think of kissing you…?”

"Do you… really think those things, Y/N?“ he said more confidently than any Shuichi Saihara you’ve ever known. His eyes sparkled, reflecting the yellow glow of the overhead lighting in his hazel-grey eyes. He stood from his seated position as well, moving closer to you until your eyes were level with his. You looked to his chest, taking a few nervous steps back.

"Y-yeah, Shuichi…” You turned away, almost sad that he never recognized your feelings… in all those years as best friends, “I always have…“ You sighed in disappointment. "I gotta… I’m gonna head to bed, now… thanks for agreeing to be my partner tomorrow.” You started to walk with your book under your armpit. His eyes almost teared up at the confirmation in your words. You returned the feelings he had felt for you for so long.

"Well, hey, hey wait!“ He grabbed your arm tightly, then earning a startled look, released it, “I can… let me walk you to your room.” It was as if your words had changed a boy into a man. It was as if all the shyness and uncertainty in him was gone, and he now spoke confidently, without a stutter to be heard. You nodded, and the two of you began to walk slowly, side by side.

Moments later you were at the dorms, standing in front of your bedroom door. You opened it, yawning slightly.

"Well, here we are… thanks again, Shuichi.“ He nodded and as he turned to leave, he halted in his tracks. You stood in the doorway, watching. Seeing you standing there, your form illuminated by the light from the dorm’s central area, he returned to himself. His nervous, boyish demeanor that you loved had overtaken him once again. You could almost see the old Shuichi come back to you as you unzipped the jacket of your uniform and rubbed the back of your sore neck. Your beauty stunned him so much that he could feel his palms get sweaty.

"Y-you know…” He turned around. “They were really lucky… the one who got your first kiss,” he stately plainly, then his tone softened.“I k-kinda… I kinda envy them.” He walked closer to you, and you took a few steps back. He advanced reluctantly until he stood in your door frame, you now in the darkness of your room. “I just wish… I wish I- I would’ve told you how I feel about you… a long time ago… then that lucky person… could’ve been me.”

“Shuichi…“ You teared up, speaking breathlessly, “I-”

“G-goodnight, Y/N…”

"Shuichi!“ You grabbed the collar of his jacket firmly in both hands, and pulled him down onto your heated lips. ”… I lied,“ You parted from his lips to whisper this one quick confession, before pushing your lips onto his once again.

"MMMHH!” His shocked and startled cry was muffled by his lips on yours. His eyes widened, but then, seeing your closed ones, seeing your passion and letting it register that his feelings for you were mutual, he let himself melt into your kiss. His long lashes fluttered as he moaned into your mouth. He edged you both forward, never unlocking your lips, until you were both fully into the room and he pushed the door closed behind him. Leaning back against it, his knees almost gave out with the intense beating of his heart. You swore you could almost hear it and could certainly feel it as he pulled you into his chest.

He trailed a shaking hand up your thigh to your waist and pulled you even closer until all of your weight rested on him. His other hand found purchase in your hair, tugging at your scalp slightly with nervous fingers. You hissed, and his body began to heat up. His skin was on fire as every sound you made turned him on further. His breath became shaky, and he could feel his pants get a bit tighter. You could feel him harden against your thigh.

"Mmm…“ he groaned, separating from you and pushing you back gently. He reddened in embarrassment. He looked down at the tent in his pants then up at you, his lip quivering in shame. This had never happened before… at least, no one had ever noticed…

"Shuichi…” You looked at him with sympathy and compassion,“It’s ok, you don’t have to be embarrassed.” But he wasn’t convinced. He looked to the floor, avoiding your gaze. “Hey…” You moved closer, taking his face in your hands and forcing him to look at you, “It’s ok…” You kissed his cheek, then placed a peck on his mouth. He kissed back softly, clearly distracted and still not fully into it. You leaned up to his ear and whispered, sending chills down his back:

"Shuichi… I love you.“ 

A small gasp left his lips. Now this was a word that was unfamiliar to him, at least, in this context. He never in a million years expected to hear it from your lips of all people. He looked to you, then, with a look of pure ecstasy, crushed his lips against yours again. You moaned into him, and with love backing his bravery, he slipped his tongue into your parted, wet lips.

"Shuichi!” You gasped in surprise at his daring move as his tongue filled your mouth. He grunted, pulling you closer as you let your tongue slide over his. Your hand reached back and slowly pulled at his soft hair, letting the silky strands fall into your hands. He moaned, pushing you back with him until you fell back onto your bed, and he fell on top of you. Climbing over you, he never let your mouths part. He threw off his jacket then pulled yours off in rapid succession.

Too lost in his overwhelming passion, his shaking hands reached down to unbutton your undershirt. Sudden nervousness and uncertainty filled you.

"Shuichi, wait…“ Your words never reached him in his frenzy. He threw the shirt off of you and brought his lips down to your neck. "Shuuu…ichi~!” You sighed as he sucked lightly at the base of your neck, then trailed kisses down your collarbone. He began to play with the edge of your pants. Warning signals flashed in your head as you grabbed his hair. “Shuichi, wait!!”

He let go of you and sat back on his knees, looking down at your half-naked body for the first time. His lusty eyes softened as he noticed the sweat that gleamed on your body, the heavy rising and falling of your chest, and the panicked expression on your face.

"Oh… Y/N, I’m so sorry.“ He looked down, his brow furrowing. "I- I didn’t mean to-”

"Shuichi, no, no it’s ok…“ You pulled him back down on top of you until his face hovered above yours. You kissed his nose. "This makes me kinda nervous, I just wanted to stop you before you got any further. I just wanna go a little slower… I mean I’ve never…”

"Me either.“ He whispered.

"Well, that I figured.” You giggled.

"Hey!“ He feigned an insulted expression. You kissed him again. He looked around. "Maybe… w-we shouldn’t be doing this.” He looked distressed. He had absolutely no experience in this field and didn’t know if he’d ever be ready. He saw your saddened face and realized that you were hurt by his words.“No, no! It’s no that I don’t want to do this with you… it’s just that,” he sighed,“ Like I said, I’ve never done anything like this and I don’t wanna… I-I don’t wanna m-mess up or hurt you.” He looked down at your face. The expression you now wore was unreadable and emotionless, and it stressed him out not knowing what you were thinking, so he asked: “A-are you sure you want to do this?” His hand rubbed up and down your thigh. You wrapped your arms around his neck.

"That’s so sweet that you are concerned about me,” you whispered faintly. Like you had mentioned before, in this killing game, you could be dead at any time, on any day, anywhere, so you had to take these opportunities before you lose them forever, and savor and cherish them. You may never get the chance to make love again. For all you know you could be murdered tomorrow, so why not spend this night with the boy you loved, before it was too late? “Yes, I do want this… do you?” He couldn’t even believe you had to ask. He wanted this so badly. He had waited too long for this perfect feeling with the perfect lover. He nodded enthusiastically.

"Of course I want you~ “ He growled, nuzzling into your neck, and grinding his erection against your hip. You inhaled sharply, a bit taken aback.

"Okay… well just go easy on me. I’m a pretty tough cookie. I’ll be okay I think. I’m just a little scared…” Little did you know that he was ten times as terrified at the thought of ruining your first time. You smiled to soothe his anxious nerves. He kissed your forehead as a sign of understanding, then began to untuck his dress shirt from his pants. He threw it over his head and onto the floor, before reaching for you again. He didn’t really know how this was supposed to go, or if he was even doing this right and being romantic, so he just winged it and hoped he was doing well.

You gasped at the chill breeze of air that wafted onto your now uncovered lower half as he shimmied your pants and undergarments down. He stared at you with glassy eyes, taking in your nude beauty with uncontrollable desire. You covered yourself with your arms, burning up.

"S-Shuichi… don’t stare!“ He looked up at your little pout and chuckled.

"Heh, I’m sorry, Y/N,” but before you could scold him for laughing he had already moved your hands away and began to suck at your collarbone again.

"Mmmmhh, Shuichi~“ you mumbled as he moved down to your chest, taking one of your now hardened nipples his mouth. You gasped, a bit shocked that your timid boy had just done that all on his own, but that gasp shifted into a yelp as he sucked a bit harder and nibbled. Your skin pulsated and you could feel your lower regions become moist and warm. Your legs squirmed, determined to let your core breath. As if reading your mind, Shuichi trailed kisses down your stomach, tickling your jumpy hips, to give your lower regions attention. He looked up to you as if to ask permission. When you nodded, he pressed his lips to your inner thigh, right at the crux of your sex.

Suddenly, you felt embarrassed again as he began to lick and bite. He smirked, feeling you twitch. He loved the feeling of knowing he caused that to happen, and the tent in his pants grew thicker, and almost painful. 

You watched as he stood and unbuckled the offending article of clothing. He pulled them down, along with his boxer-briefs and sucked in a breath of relief as he sprang free.

He crawled back on top of you, placing his elbows on either side of your head. He spit into his hand, knowing at least this much about sexual intercourse, and used his saliva to lubricate your entrance thoroughly. You could now feel his hot, firm member against your naked thigh. You looked down at it, then looked back up at his face, clearly distressed.

"Wha-what’s wrong, Y/N?” He caressed your face with his pale, soft hand.

"N-nothing…“

"Something’s wrong. What did I do? Do you wanna stop now?” He shot out concerned, rapid-fire questions before you could even answer the first one.

"No! No I just…“ He got it now.

"Oh! …oh,” He looked down, “Is it not big enough?” He looked disappointed.

“Shuichi!” You almost laughed. “I can’t believe you think that’s the problem. It’s quite the opposite, actually…” He cracked that crooked, awkward smile, reassured by your words. “I just think… I mean,” before he could say what you knew he was going to say, you cut him off, “NO! I do not wanna stop, Shuichi, ” You shook your head, chuckling at how sweet he was.

It was times like this that made you realize just how exaggeratedly and unrealistically the novels and stories you’ve read portrayed romance. In stories, the couples always had the perfect first love scene. Their first time went off without a hitch. It was flawless, rhythmic, sensual, and seemed too romantic and perfect to be true. Well, that’s because it was. You now knew that no one is an expert their first time, and the awkward, shy, imperfect love between two partners who share their first time is what made it more beautiful than any fictional story could ever recreate. Here you were, with the boy you loved. He wasn’t very skilled, and not very romantic, but you wouldn’t want it any other way.

"Well, I don’t wanna hurt you, Y/N"

"I know, Shuichi. I’ll be okay… just…“

"I’ll go slow, ok?” You nodded. He took both of your hands in his, holding them firmly. He looked at you, and when he saw a sure nod of approval, he place himself at your entrance. “Ok, just squeeze my hand if it hurts, ok?” You nodded. He kissed your nose, as if to apologize for the pain he would cause you momentarily. Slowly, he pushed the tip. He grimaced at the tightness he could already feel.

You shifted slightly, feeling more discomfort than actual pain. Like an annoying itch or sting. But then he pushed in the rest of the way. There was a tight burning, and you gasped loudly. Your hand squeezed his and shook violently. His eyes flashed up to yours in worry when he heard that gasp.

"Ngh!“ Your teeth clenched as a rogue tear rolled down your face.

"Oh no, oh no, Y/N!” He kissed your cheeks over and over, salty drops falling down his own cheeks now, “I am so, so sorry,“ His voice shook and crackled. "I’m so sorry, Y/N!” He peppered your neck with light kisses.

"I-It’s ok-kay, Shuichi,“ You tried to hold in tears. Every time he shifted his weight, his member felt like it was tearing your insides a tiny bit more. It sent a jolt of dull pain up your spine. "J-just, move slowly.” He nodded, and without another word, obeyed. 

He began to slowly pull himself out to the tip, then ease back in, earning another hiss from you. He grimaced again. He did this same motion again, and the first few times still felt a little weird and uncomfortable for you. He kept going at this unbearably slow rate, looking for a reaction from you.

"Ah…“ You let out a small whimper as the stinging was slowly replaced with… something else. He heard this noise and the corner of his mouth lifted, moving out and back in again. "Mmmh,” You mewled. “Shuichi, go faster.” He looked at you with doubtful eyes.

"Are you sure?“

"Yes, please, Shucihi,” you pleaded. He began to quicken his pace, still going far too slow for his own liking, as if his mind was telling him to pound into you, but his heart said slow down. “Mmmmhh…” You moaned. Shuichi sped up a little more.

"Ah~“ Shuichi let out a little groan. Now he was starting to feel that pressure build in the pit of his stomach, and he wanted more. He went faster. You whined, calling out his name. He brought himself down, until all of his weight was on you, and sped up again.

"Shuichi~!” Your nails raked down his back, causing him to hiss as he breathed hot, labored air into your ear. He could feel your own heartbeat on his chest and hear you breath hitching. You struggled for air, feeling a pleasure you’d never come even close to feeling before. His sweat covered body wet the hair on the back of his neck and on his forehead, and you ran your hand through it roughly. The feeling slowly grew like a mounting climax.

Shuichi reached one shaking hand down to grab your leg. Hooking his hand under your thigh, he bent it up and over his shoulder, plunging deeper into you at the new angle. 

"Shuichi!“ You yelled his name into his hair as the new position caused him to hit a spot you didn’t know existed. Every thrust built and built up, and Shuichi’s groans in your ear became louder. He scraped the very back of your walls with every new buck of his hips.

"Y/N! I-” he could hardly speak, but began to pound into you as fast and hard as he could. It felt so amazing that you couldn’t even express it. Your mouth just hung open as your vision blurred, almost at your limit.

“Shu-i-chiiii~ ah!“ It was all too overwhelming. The pressure in your lower abdomen released like a spring, and exploded in a thrilling climax. Your legs began to shake and your senses all heightened at once. Shuichi gasped, feeling you tighten around his member and your own fluids coating you both. Already close, this sent him over the edge as well. He moaned, and with a few last sloppy thrusts, you felt him pulsate and release into you. His voice was stressed, hoarse, and cracked like the nerdy boy you knew and loved as he made squeaking and moaning noises.

He collapsed on top of your body. You couldn’t even feel his weight, as you were almost numb, coming down from your own high. Your legs still trembled, and you both breathed raggedly with very little energy left. He lifted his droopy eyes to you.

"Are… are you okay?” he asked with genuine concern. You couldn’t even think about a proper response, so you just sloppily kissed his lips with what all you had left. He took that as a yes, and grinned, rolling off of you to the side. He grabbed his discarded shirt beside the bed and used it to quickly clean you both off as much as he could.

Shuichi pulled your blankets over the both of you and pulled you in against him. He kissed your head as you began to drift off to a much needed sleep.

"I love you too, Y/N.” he whispered to your drowsy form. “I’m a lucky man.”


End file.
